


I'll Bet That Taking A Risk Is Worth It

by delinquentdee



Category: Arrow (TV 2012)
Genre: Alternate Universe - Different First Meeting, Alternative Universe - No Island, F/M, Thea & Felicity Friendship, thea is a typical little sister
Language: English
Status: Completed
Published: 2017-02-18
Updated: 2017-02-18
Packaged: 2018-09-25 07:26:20
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,195
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9809246
Author URL: https://archiveofourown.org/users/delinquentdee/pseuds/delinquentdee
Summary: Not everyone from Vegas enjoys gambling. But maybe, if Oliver plays his cards right- and Thea shuts her mouth- Felicity might be willing to take a chance on him.





	

For a Vegas girl, Felicity wasn’t much of a gambler. Perhaps it was the ingrained reminder that “the house always wins” which colored her thinking. When she was in the first grade, her teacher Miss McManus told her she would be eligible to compete in the Mathbee - _ with the third graders!- _ if she worked harder on her time-telling skills. Never was there a more determined little girl in the whole of Staton Elementary School. Felicity decided to take a wall clock with her everywhere, despite her mother Donna’s attempts at a wristwatch and even a Flava Flave inspired necklace. Felicity sat at the bar where her mother worked, staring intently at her traveling clock. She was trying to figure out what time it would be if 93 minutes passed. With her hands balled into fists, in order to gain the habit of not counting on her fingers, and blue eyes intent behind glasses, she watched as a pit boss snatched the learning tool away, grumbling, “No clocks, kid.”

While Felicity didn’t learn what time an additional 93 minutes would lead to, she did learn the sliminess that was involved in Vegas casinos.

“No clocks and no windows, peach. If they know what time it is, they’ll want to leave,” Marco told her. She was confused, to say the least.

“But what if they miss their bed time?” Marco’s face morphed into a sickly smile. “that just means that they put more money in our pockets.”

Gambling outside casinos wasn’t any better. She once watched a man lose sixty grand over a bet on which wet paper towel would fall from a ceiling first.

The addictive nature of a bet was not something Felicity could ever understand. Risks and gambles were avoided… until they weren’t.

With a brief glimpse into her life as a first grader, it could be assumed that Felicity was a star pupil. That assumption would be mostly correct. She spent elementary, middle, and a good deal of high school as a proper incident-less student. Her final year brought about a rebellious streak, complete with darkened hair, lipstick, and nail polish. This lasted through a hefty majority of her university years where her “goth/punk aesthetic” found its way into her mentality, aided by a less than stellar relationship with a certain Cooper Seldon.

Felicity found herself as being a “quiet heckler”, sitting in the back row with her boyfriend and  their his friends, telling jokes at the expense of their professors. They were the stereotypical hubris-filled young geniuses. Cooper’s epic fuckup where he managed to lose his admittance to MIT, his friends, and his girlfriend, brought about a change in Felicity.

She may have ditched the Elvira look, but the confidence that she gained by dressing that way remained with her. By looking dark and dangerous, Felicity allowed herself to act that way.

Post-Cooper, Felicity was eager to find herself; to have a look that reflected her personality instead of the other way around.

Not all of the goth went down the drain with her black hair dye. She still felt restless in some of the slower classes she took, specifically an app making course.  _ Why _ an app making class was required for a degree in cyber security, her advisor was never able to answer.

Her professor was the type of man to use outdated memes to try and connect with the class. While it should have come off as endearing, Felicity was nothing but irritated by the course.

While other students spent months pouring over their work, the time she set aside for her final was lacking. Felicity knew she wasn’t giving it the time or effort it deserved, and for the first time in a long time, she took a risk.

A night of brainstorm drinking and running into a box of Cooper’s belongings was the cause for her inspiration.

She called it REFL _ ex _ ION, an app to rate your exes. Was it petty? Yes. Was it stupid? Kind of, yes. Was it something she believed could and would be used by her peers? Abso-frigging-lutely. Absolutely.

She didn’t get full marks for her work. Or rather, she didn’t  _ just _ get full marks for her creation. She became an overnight sensation.

She took a risk, and somehow landed herself in Starling City serving as the headquarters to a multimillion dollar collection of dating/breaking up apps.

REFL _ ex _ ION wasn’t a hate fest. In order to leave a review, it was necessary to leave a positive assessment as well. From there came the addition of the dating app. Felicity had a think tank. She had employees whose job it was to think of new ideas. How did her plan of becoming a security specialist turn into this life? She wasn’t complaining- how could she? She was a rich and successful woman and despite her irritation with the app making class, she genuinely enjoyed her work. It was just different. Unexpected. The odds of this happening were quite low. She wouldn’t have bet on it even if she  _ were  _ a gambling woman.

→♥←

For a wealthy and attractive man, Oliver hadn’t had as many partners as you would think. That’s not to say that his, uh,  _ companionship _ was sparse. He had a bit of a reputation as a playboy, highly inflated by gossip rags. Apparently if he was seen out anywhere with a woman, he must be pursuing a sexual relationship. That just wasn’t true… anymore.

It took a while, but Oliver believes he has grown up. Whether or not that’s a thought bona fide adults have is up for question. The dissolution of his parents’ marriage somehow brought about a new Oliver Queen. One that was thoughtful and caring, career oriented and focused. He made it his duty to be there for his heartbroken little sister Thea. No matter how clean the separation was, it was too painful for wholesome twelve-year-old. It was his mother that suggested he take an active role in the family company. Thea was under the belief that her father was the villain, turning against his wife and deserting the family- which was wholeheartedly NOT the case.

Over time Thea was able to accept her parents’ search for their own happiness outside of the family they built together. The tears that Thea cried at her mother’s wedding to long time Queen Consolidated COO Walter Steele were of joy, not anger. While Thea found that families don’t necessarily break from a divorce, Oliver learned that he had a great skill for diplomacy and negotiation. What started as a tactic to make his sister feel better turned into a career he actually found himself enjoying.

→♥←

Oliver and Thea sat across from each other at the SC Jitters on Morrissey and Smith, as per Thea’s request.

There was no other way to describe Thea’s countenance other than _ jittery _ , and she didn’t even take a sip from her latte yet.

After a few minutes of awkward silence, Oliver decided to take the plunge. “Everything okay Speedy?”

The snarl that made way onto Thea’s face was a brief moment of relief. She finally caught his eye.

She nodded her head a few times before swallowing deeply. “You know you can talk to me about anything, right Ollie.”

Oliver raised an eyebrow. “I’m pretty sure that was going to say that to you.”

At her agitated lip bite, Oliver pushed again. “It’s been a while since I attempted to follow the thought process of a teenaged girl, but I’m pretty sure this is you projecting your issues onto me. So is there something you need to talk to  _ me  _ about? Because you know I’m always here for you.”

Thea’s index finger traced the rim of her mug, eyes following the movement. “I’ve just been questioning some stuff lately.”

Oliver forced a blank face. Too much inquisition could push her away and exasperation at her lack of response was sure as hell not going to get him anywhere.

“What kind of stuff.” He took a sip from his own cup, feigning an air of nonchalance.

Her head popped up and tilted. She nodded her head towards him, eyes opening more deliberately and eyebrows rising to accommodate the space those huge green orbs took up on her forehead. “Questioning, Ollie.”

He wracked his brain to find some meaning between her actions and words, when it clicked.

“Thea, I love you no matter what, but maybe this is a better conversation for Sara? Not that I can’t help you out! But just maybe she can offer you better clarity or something.”

So much for the calm and collected corporate Oliver Queen.

Thea’s hands popped up as if she could physically stop his thought process. “Woah, slow down. I was trying to subtly ask you if you’re gay.”

When he agreed to meet her this morning, he genuinely assumed she just wanted some sibling time, but instead she booked two tickets on a crazy train.

Words escaped him. “Thea. How? No, what? I mean-“

She twirled some hair between her fingers. “Don’t act like it’s crazy. You had your crazy younger years, which I guess was you trying to find yourself and now you’re like perpetually single. And you know what they say.”

She waved her hand at him as if she expected him to know what she was alluding to.

“I don’t actually know what they say. I’m not even sure who ‘they’ is that you’re talking about.”

“The universal ‘they’, Ollie. And what it is they say is, ‘All the good ones are either taken or gay.’”

Oliver adjusted his tie. “So let me get this straight. You’re questioning my sexuality based on a cliché?”

She sat back in her seat with a sigh. “Well, when you say it like that it sounds stupid.”

“Is it just when I say it, or when hearing it out loud.”

“Bit of both actually.”

He chuckled just now realizing how much he missed having Speedy around. “For clarification: I’m straight, I’d love you no matter who you choose to be with, and clichés are not meant to be taken as truths.”

Oliver was too focused on his sister’s smiling face that he was genuinely surprised when a brilliantly radiant blonde stepped up to their table.

Felicity smiled brightly at Oliver, “Actually I’m pretty sure that one definition of a cliché is, ‘a universally accepted truth’. Or something like that.”

_ Smart too _ , was his initial reaction. Somewhere in the back of his mind he recognized that he should be highly irritated by a stranger correcting him, but he couldn’t bring that fleeting thought to the forefront of his mind.

Her smile morphed instantaneously into a look of horror and shame that Oliver didn’t find unattractive at all. It gave bit of color on her cheeks.

“Oh my god, I’m so sorry. That was incredibly rude. I wasn’t listening in on your conversation. Purposefully. I wasn’t purposefully listening to you. It’s just that my pen rolled under your table. I meant to just come over and ask for it, but clearly I should be banned from all human interaction.” Her hands were all over the place.

Thea was too stunned by Felicity’s outburst to have any reaction. Oliver too was stunned, but was in no way eager to stop her rambling.

“Though I don’t know if I would consider you guys human. You’re both kind of god like. Highly attractive, you know.” He watched her take a deep breath and realize what words actually came out of her mouth.

She jutted her thumb behind her. “I’m just going to leave. I’m sorry. No dollar store pen is worth this embarrassment.”

Before she could walk away, Thea shouted out. “Hey wait, I got it!” While Thea rummaged under the table, Felicity tried her hardest to avoid making eye contact with Oliver.

He opened his mouth, not sure what exactly was going to come out of his mouth, but not caring about that either. Anything to get her attention back on him.

Before he had the chance to speak, Thea popped from below the table, red pen in hand.

“Oh thank God!” The relief was clear in her voice and eyes.

Before she had a chance to walk away, Thea spoke up. “You seem pretty intelligent.”

Felicity, thinking it was the beginning of a telling off blushed deeply. “The clumsy comes along with the brains. Not always, but very much in this case.”

Oliver found his voice. “And where does the adorable fit in?” It was clear he caught her off guard. He surprised himself with that one, too.

“It’s probably a hallucination. Most likely some adverse reaction to your coffee, because this,” she pointed to herself, “is all awkward and exhausted from work.”

Thea giggled. “Please, come sit. Do you think you could help us out,” Thea left her sentence hanging, in a plea for the blonde’s name.

“Felicity. Smoak. Felicity Smoak.” She pointed to herself with the pen.

Thea gave a small wave. “I’m Thea, and this is my brother Oliver.”

Felicity gave a cute little bobble of her head, unsure what Thea was getting to.

“Your assistance with clichés is much needed.”

Oliver, having known his sister for the entirety of her life, knew what she was up to. “Thea,” he warned.

But Thea paid him no mind. “Do you believe clichés?”

Felicity tilted her head, a low “Hmm” heard from her throat.

“Depends on the cliché, I suppose. Any one in particular I can give my confirmation on?”

The devilish look passed in Thea’s eyes. “How about the one that claims all the good eligible guys are either married or gay?”

Felicity scrunched up her nose. “I have a hard time believing that one.”

Thea attempted to make her eyes as doe like and innocent as possible. “You should definitely question how valid it is when I have the exception sitting across from me.”

Felicity, looking intrigued, cast her eyes over to Oliver.

“Do you often use your sister to pick up women?”

Oliver gave a deep laugh. “I can honestly say that I haven’t done that in at least a decade. Plus, it never really works when your little sister is the devil incarnate.”

Her eyes zipped over to Thea. “He calls you the devil, and yet you call him a ‘good one’? I must be missing something here.”

Thea grinned. “Intriguing, isn’t it. Maybe you guys should talk it over some dinner.”

Felicity looked at Thea with awe apparent on her face. “Do you have a line for everything?”

Thea shrugged, playing coy.

“I’d like to say she picked it up from me, but I don’t think I was ever that smooth.”

The corner of Felicity’s mouth ticked up. “I find that very hard to believe. I’d be more likely to believe that Google was going under, to be quite honest.”

Thea perked up out of nowhere.

“Google!” She dug her phone out and started tapping furiously.

“Oliver, you need to step your game up. Your sister has totally managed to win me over. She can successfully chat me up and shows genuine interest in possibly the greatest company ever.”

“Is that what it takes to please you, some cheap lines and not using Bing? Because I’ve got to say, if that’s it, I’m no longer intimidated.”

Her blush was so alluring. Before she could respond, Thea’s laugh broke their connection.

“Oh no, maybe I should’ve checked your stats before I tried to convince Felicity that she wanted to date you.”

Oliver’s eyes squinted, “Stats?”

“Yeah. I Googled you and ‘why is he single’, and you popped up on this Rate My Ex app. Turns out, you’re not dating material. A love ‘em and leave ‘em kind of guy. I might need to bleach my eyes after reading some of those comments.”

He was too focused on Thea and her findings to see the shell shocked expression on Felicity’s face.

“What app is that?” He asked grabbing for her phone.

Thea slapped away his hands while Felicity spoke up.

“I’m going to have to take credit for that, sorry.”

Oliver managed to grab the device from his sister while Thea kicked him under the table yet still acknowledging Felicity’s declaration.

“What’s that mean?”

Felicity bit her lip. “I kind of developed that app in college.”

Both Queen siblings snapped their heads towards her.

“Sorry about that.”

Oliver laughed, causing Felicity to sigh in relief. “I was always a little iffy about it, because it can turn so nasty so quick. But there was an exec in my class watching our presentations and he really encouraged me to put it on the market so I did. I make other cooler apps! Dating apps that aren’t at all focused on,” she gestured towards Thea’s phone, “That. And a cool trivia game too!”

With challenging eyes, he asked, “Does company policy keep you from making a dating app profile?”

Never one to cower, Felicity answered honestly, “Actually, PR insists that I have a profile for myself. Planning on joining?”

“If it helps me search for you.”

Felicity wagged her finger. “Sorry buddy, there isn’t an option for that. You match with whoever you have in common. This isn’t Facebook.”

He gave her a nod. “Okay then, how about we cut out the middleman, and we exchange numbers here so we can set up a date?”

Felicity pouted. “Don’t discount my middleman. There’s some fantastic algorithms in effect on there that determine compatibility. You and I could clash terribly, you never know.”

“So we go out on a date and see if we’re suitable. Try it old school.”

“Hey, I happen to like technology. I create apps for a living, I’ll have you remember. Besides,” she said, a teasing lilt in her voice, “Your REFL _ ex _ ION score is pretty terrible.”

He reached across the table and grabbed her hand. “Take a chance on me.”

She stared at their hands together, both of them completely unaware of Thea who was most likely recording the entire conversation. “I’m not much of a risk taker, Oliver. Growing up in Vegas does that to you.”

He rubbed his thumb across her knuckles. Trying to coax her into agreeing.

She looked up and their eyes connected. She saw sincerity and a dash of desperation.

“But, maybe this can be one of the rare occasions where I take a gamble.”

Thea, for some reason far beyond Oliver’s understanding, didn’t sit quietly like the good little sister he hoped for. “Being safe is prudent, but not very fun or fufilling.”

He was about to tell her to mind her own business when Felicity chortled. “I suppose I have to now. Thea, you’re very convincing and Oliver is fortunate to have such a gifted wing woman.”

Thea flipped her hair behind her ear. “I do what I can.”

Felicity covered their joined hands with her free one. “Okay, Oliver it’s your lucky day. I want to be unsafe with you.”

Before Oliver could respond Felicity’s face scrunched up in pain and slammed her hand to her head. “Please lie and say that only sounded sexual to me.”

**Author's Note:**

> If you take anything from this story, I hope it's that little sisters are fantastic. Because we totally 100% are the best things that could happen to older siblings. Thanks for reading !!


End file.
